700-58-3

Basic information

• Product Name: 2-Adamantanone
• Synonyms: Adamantan-10-one;Adamantan-9-one;Tricyclo[3.3.1.13,7]decane-10-one;2-adamandanone;2-Adamantanone,98%;Tricyclo[3.3.1.1~3,7~]decan-2-one, 2-Oxotricyclo[3.3.1.1~3,7~]decane;2-AdaMantane Ketone;2-ADAMANTANONE FOR SYNTHESIS 5 G
• CAS NO: 700-58-3
• Molecular Formula: C₁₀H₁₄O
• Molecular Weight: 150.22
• EINECS: 211-847-2
• Product Categories: Adamantane derivatives;Adamantanes;Ring Systems;C10;Carbonyl Compounds;Ketones;Building Blocks;Carbonyl Compounds;Chemical Synthesis;Organic Building Blocks;Adamantane Derivative;FINE Chemical & INTERMEDIATES
• Mol File: 700-58-3.mol
• Article Data: 376

Chemical Properties

• Melting Point: 256-258 °C (subl.)(lit.)
• Boiling Point: 211.78°C (rough estimate)
• Flash Point: 95.7 °C
• Appearance: White to off-white/Crystalline Powder
• Density: 0.8709 (rough estimate)
• Vapor Pressure: 0.0267mmHg at 25°C
• Refractive Index: 1.4993 (estimate)
• Storage Temp.: Store below +30°C.
• Solubility: methanol: 0.1 g/mL, clear
• BRN: 1210235
• CAS DataBase Reference: 2-Adamantanone(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Adamantanone(700-58-3)
• EPA Substance Registry System: 2-Adamantanone(700-58-3)

Safety Data

• Hazard Codes: Xi
• Statements: 52-36/37/38
• Safety Statements: 22-24/25-36-26
• WGK Germany: 2
• RTECS: AU5018000
• Hazardous Substances Data: 700-58-3(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 700-58-3 differently. You can refer to the following data:
1. 2-Adamantanone has been used as a probe for the dimensions and characteristics for the substrate binding pocket of alcohol dehydrogenases.
2. 2-Adamantanone was used in the synthesis of dispiro N-Boc-protected 1,2,4-trioxane and (+/-)-1-(adamantan-2-yl)-2-propanamine.

synthesis

Dissolve the alcohol (0.25 mmol) in acetonitrile (3 mL). Add oxidant 1,3-dichloro-5,5-dimethylhydantoin (DCH, 0.148 g, 0.75 mmol) to the reaction mixture. Add the pre-catalyst MWCNT-{(CH2)3-CO- NH-TEMPO}n (0.075 g) to the reaction mixture. Sonic the resulting suspension (1 min.) using an ultrasonic bath. Stir the reaction mixture. Heat the reaction mixture at 50 °C for 30 minutes. Filter the reaction mixture. Add CH2Cl2 (10 mL) to the reaction mixture. Wash the organic phase with aqueous Na2S2O3 (10 %, 10 mL) and H2O (10 mL x 2). Dry the residue with Na2SO4. Remove the solvent under reduced pressure using a rotary evaporator to obtain the product.

Chemical Properties

white to off-white crystalline powder with camphor smell, soluble in methanol, ethanol, DMSO and other organic solvents, from synthesis.

General Description

2-Adamantanone on deprotonation in the gas phase affords the corresponding β-enolate anion. It reacts with 1,1-dilithio-1-sila-2,3,4,5-tetraphenylsilole to yield 5-silafulvene.

Purification Methods

Purify 2-admantanone by repeated sublimation in vacuo. [Butler et al. J Chem Soc, Faraday Trans II 82 535 1986.]

InChI:InChI=1/C10H14O/c11-10-8-2-6-1-7(4-8)5-9(10)3-6/h6-9H,1-5H2

Synthetic route

1-adamantanol (700-57-2) → 2-Adamantanone (700-58-3)

Conditions	Yield
With ferric nitrate; barium(II) chloride at 90℃; for 0.666667h;	100%
With ruthenium trichloride; iodobenzene; potassium peroxomonosulfate In water; acetonitrile at 20℃; for 0.8h;	100%
With ruthenium trichloride; iodobenzene; potassium peroxymonosulfate In water; acetonitrile at 20℃; for 0.8h; Inert atmosphere;	100%

adamantane (281-23-2) → 2-Adamantanone (700-58-3) + 1-adamanthanol (768-95-6) + 1,3-adamantandiol (5001-18-3)

Conditions	Yield
With methyltrifluoromethyldioxirane In dichloromethane at -22℃; for 0.0166667h;	A n/a B n/a C 86%
With 6-chloro-4-trifluoromethyl-1,2,3-benzoxathiazine-2,2-dioxide; urea hydrogen peroxide adduct; bis[3,5-bis(trifluoromethyl)diphenyl] diselenide In 1,2-dichloro-ethane at 22℃; for 95h;	A n/a B 80% C 5%
With tetrabutylammomium bromide; oxygen; N-hydroxyphthalimide In water at 80℃; under 760 Torr; for 6h; Product distribution; further additives, solvents;	A 12% B 60% C 23%

adamantane (281-23-2) → 2-Adamantanone (700-58-3) + 1-adamanthanol (768-95-6)

Conditions	Yield
With pyridine; bis(acetylacetonate)oxovanadium; dihydrogen peroxide; Hexafluoroacetone In water at 60℃; Catalytic behavior; Temperature; Reagent/catalyst;	A 70% B n/a
With tetrachloromethane; tetrabutylammomium bromide; water; molybdenum hexacarbonyl at 140℃; for 13h; Inert atmosphere;	A 66% B 34%
With sodium periodate; ruthenium(IV) oxide In tetrachloromethane; water; acetonitrile at 20℃; for 19h;	A 1.6% B 62%

2-adamantanone oxime (4500-12-3) → 2-Adamantanone (700-58-3)

Conditions	Yield
With tris[trinitratocerium(IV)] paraperiodate at 90℃; for 0.25h;	95%
With ruthenium trichloride; toluene-4-sulfonic acid In N,N-dimethyl acetamide; water at 120℃; under 760.051 Torr; for 14h; Inert atmosphere; Green chemistry;	95%
With L-alanin; silica gel; chlorochromic acid In dichloromethane at 20℃; for 9h;	90%
Multi-step reaction with 2 steps 1: 1.) sodium nitrite, AcOH, 2.) NaBH4 / 1.) CH2Cl2, room temperature, 4 h, 2.) EtOH, room temperature, 1 h 2: 33 percent / 1 h / 160 °C View Scheme
With gold(III) tribromide; dimethylglyoxal In ethanol; water at 20℃; for 15h; pH=7;	100 %Spectr.

adamantane-2-spiro-3′-1′,2′,4′,5′,7′-pentaoxocane + 1,2-diamino-benzene (95-54-5) → 2-Adamantanone (700-58-3) + 2Н,5Н-1,6-(methanedioxymethano)benzo[e][1,2,4,7]dioxadiazocine

Conditions	Yield
With samarium(III) nitrate hexahydrate In tetrahydrofuran at 20℃; for 6h; Inert atmosphere;	A n/a B 60%

adamantane (281-23-2) → 2-Adamantanone (700-58-3) + 1-adamanthanol (768-95-6) + 1-adamantanol (700-57-2)

Conditions	Yield
With [2,2]bipyridinyl; Ba; trifluoroacetic acid In dichloromethane at 20℃; for 0.0333333h; Product distribution;	A n/a B 97% C n/a
With [2,2]bipyridinyl; Ba; trifluoroacetic acid In dichloromethane at 20℃; for 0.0333333h; Yields of byproduct given;	A n/a B 97% C n/a
With ammonium cerium(IV) nitrate; oxygen In acetonitrile for 5h; Ambient temperature; Irradiation;	A 5% B 85% C 5%

adamantane (281-23-2) → 2-Adamantanone (700-58-3) + 1-adamanthanol (768-95-6) + 1-adamantanol (700-57-2) + 1,3-adamantandiol (5001-18-3)

Conditions	Yield
With BaFeO(2.8-x); oxygen at 89.84℃; under 750.075 Torr; for 96h; Catalytic behavior;	A 5% B 48% C 3% D 11%
With oxygen; propionic acid; bis(acetylacetonate)oxovanadium at 120℃; under 760.051 Torr; for 6h; Product distribution / selectivity;	A 5.5% B 31.6% C 3.9% D 7.9%
With methanesulfonic acid; oxygen; propionic acid; bis(acetylacetonate)oxovanadium at 100℃; under 760.051 Torr; for 6h; Product distribution / selectivity;	A 4.2% B 25.1% C 3.9% D 2.4%

adamantane-2-thione (23695-65-0) → 2-Adamantanone (700-58-3)

Conditions	Yield
With nitrosonium tetrafluoroborate In dichloromethane for 0.5h; Ambient temperature;	94%
With ozone In diethyl ether at -70℃;	90%
With clay supported cupric nitrate In dichloromethane Ambient temperature;	68%

spiro[adamantan-2,2'-(5'-bromo-5'-methyl-1',3'-dioxolan-4'-one)] (518050-74-3) → spiro[adamantan-2,2'-(5'-methylene-1',3'-dioxolan-4'-one)] + 2-Adamantanone (700-58-3)

Conditions	Yield
With triethylamine In cyclohexane at 0 - 20℃; for 3h;	A 11% B n/a

spiro[adamantan-2,2'-(5'-methyl-1',3'-dioxolan-4'-one)] → spiro[adamantan-2,2'-(5'-bromo-5'-methyl-1',3'-dioxolan-4'-one)] (518050-74-3) + 2-Adamantanone (700-58-3)

Conditions	Yield
With N-Bromosuccinimide In cyclohexane at 80℃; for 3h;	A 8% B n/a

C20H23ClO3 → 2-Adamantanone (700-58-3)

Conditions	Yield
With N-benzyl-trimethylammonium hydroxide In tetrahydrofuran; methanol at 20℃; for 1h;	84%

C18H18F6N2 → 2-Adamantanone (700-58-3) + 1-(3,5-bis(trifluoromethyl)phenyl)-3,5-dimethylpyrazole (1526941-41-2)

Conditions	Yield
With toluene-4-sulfonic acid In ethanol at 80℃; for 24h; Inert atmosphere;	A 80% B 91%

2,2-propanediyldimercaptoadamantane → 2-Adamantanone (700-58-3)

Conditions	Yield
With nitric acid; arsenic(III) trioxide In dichloromethane at 0 - 5℃;	96%
Stage #1: 2,2-propanediyldimercaptoadamantane With chloro-trimethyl-silane; sodium iodide In acetonitrile at 60℃; for 24h; Stage #2: With water In acetonitrile for 0.0833333h;	88%

C16H19BrN2 + acetylacetone (123-54-6) → 2-Adamantanone (700-58-3) + 1-(4-bromophenyl)-3,5-dimethylpyrazole hydrochloride (1526941-40-1)

Conditions	Yield
Stage #1: C16H19BrN2; acetylacetone With toluene-4-sulfonic acid In ethanol at 80℃; for 24h; Inert atmosphere; Stage #2: With hydrogenchloride In diethyl ether Inert atmosphere;	A 86% B 86%

C17H22N2 + acetylacetone (123-54-6) → 2-Adamantanone (700-58-3) + 3,5-dimethyl-1-(o-tolyl)-1H-pyrazole (91565-80-9)

Conditions	Yield
With toluene-4-sulfonic acid In ethanol at 80℃; for 24h; Inert atmosphere;	A 92% B 91%

C16H20N2 (1526941-45-6) + acetylacetone (123-54-6) → 2-Adamantanone (700-58-3) + 3,5-dimethyl-1-phenyl-1H-pyrazole (1131-16-4)

Conditions	Yield
With toluene-4-sulfonic acid In ethanol at 80℃; for 24h; Reagent/catalyst; Inert atmosphere;	A 92% B 95%

adamantane (281-23-2) → 2-Adamantanone (700-58-3) + 4-oxohomoadamantan-5-one (21898-84-0) + 1-adamanthanol (768-95-6) + 1-adamantanol (700-57-2)

Conditions	Yield
With N-hydroxyphthalimide; ammonium cerium (IV) nitrate; oxygen In 1,2-dichloro-ethane at 40℃; for 24h;

adamantane (281-23-2) → 2-Adamantanone (700-58-3)

Conditions	Yield
With oxone; 1,1,1-trifluoro-2-propanone; sodium hydrogencarbonate In dichloromethane; water at 0 - 25℃; under 3878.71 Torr; for 0.0222222h;	98%
With potassium sulfate; sulfuric acid at 40 - 55℃; for 40h; Product distribution / selectivity;	87%
With lithium sulfate; sulfuric acid at 40 - 55℃; for 40h; Product distribution / selectivity;	87%

2-(methoxymethylene)adamantane (72590-63-7) → 2-Adamantanone (700-58-3) + tricyclo<3.3.1.13,7>decane-2-spiro-3'-(4'-methoxy-1',2'-dioxetane) (73774-49-9) + C16H27NO3Si

Conditions	Yield
With trimethylsilyl cyanide; oxygen; 5,15,10,20-tetraphenylporphyrin In dichloromethane at -70℃; Irradiation;	A 22% B 30% C 35%

adamantylidene-adamantane (30541-56-1) → 2-Adamantanone (700-58-3) + bisadamantylidene epoxide (29186-07-0)

Conditions	Yield
With oxygen In dichloromethane for 16h; Irradiation;	A 30% B 9%
With oxygen In dichloromethane Irradiation;
With chromyl nitrate In tetrachloromethane; dichloromethane; N,N-dimethyl-formamide at -78℃; for 1h; Title compound not separated from byproducts;	A 3 % Chromat. B 92 % Chromat.

3.3.1.13,7.tricyclo 2-decane 2'-spiro(1',3'-dithiolanne) (19557-70-1) → 2-Adamantanone (700-58-3)

Conditions	Yield
With (CH3)3CI; dimethyl sulfoxide for 12h;	85%
With trimethylsilyl bromide; dimethyl sulfoxide In tetrachloromethane at 75 - 80℃; for 28h;	75%

bis(adamantylidene)methane (28939-47-1) → 2-Adamantanone (700-58-3)

Conditions	Yield
With oxygen; methylene blue In dichloromethane at 15℃; for 7.5h; Irradiation;	87%

C20H24O3 → 2-Adamantanone (700-58-3)

Conditions	Yield
With sodium hydrogencarbonate In N,N,N,N,N,N-hexamethylphosphoric triamide at 20℃; for 8h;	62%

C17H22N2 + acetylacetone (123-54-6) → 2-Adamantanone (700-58-3) + 1-(4-methylphenyl)-3,5-dimethyl-1H-pyrazole (20157-46-4)

Conditions	Yield
With toluene-4-sulfonic acid In ethanol at 80℃; for 24h; Inert atmosphere;	A 80% B 84%

C16H19FN2 + acetylacetone (123-54-6) → 2-Adamantanone (700-58-3) + 1-(4-fluorophenyl)-3,5-dimethyl-1H-pyrazole (81329-48-8)

Conditions	Yield
With toluene-4-sulfonic acid In ethanol at 80℃; for 24h; Inert atmosphere;	A 90% B 84%

C21H31N3O2S + acetylacetone (123-54-6) → 2-Adamantanone (700-58-3) + 2-(3,5-dimethylpyrazol-1-yl)-N,N-diethyl-4-methylbenzenesulfonamide (1526941-42-3)

Conditions	Yield
With toluene-4-sulfonic acid In ethanol at 80℃; for 24h; Inert atmosphere;	A 87% B 84%

C14H24N2 + acetylacetone (123-54-6) → 1-butyl-3,5-dimethylpyrazole (2655-37-0) + 2-Adamantanone (700-58-3)

Conditions	Yield
With toluene-4-sulfonic acid In ethanol at 80℃; for 24h; Inert atmosphere;	A 82% B 86%

acetylacetone (123-54-6) + benzylmagnesium chloride (6921-34-2) + spiro[adamantane-2,3'-diazirine] (41736-95-2) → 2-Adamantanone (700-58-3) + 1-benzyl-3,5-dimethyl-1H-pyrazole (1134-81-2)

Conditions	Yield
Stage #1: benzylmagnesium chloride; spiro[adamantane-2,3'-diazirine] In diethyl ether at 0℃; for 2h; Inert atmosphere; Stage #2: acetylacetone With toluene-4-sulfonic acid In ethanol at 80℃; for 24h; Inert atmosphere;	A 84% B 100%

adamantane (281-23-2) + 3,3-dimethyldioxirane (74087-85-7) → 2-Adamantanone (700-58-3) + 1-adamanthanol (768-95-6) + 1-adamantanol (700-57-2)

Conditions	Yield
In acetone at 22℃; for 18h; protected from light;	A n/a B 87% C n/a

2-adamantylidene-N-tert-butylaziridine (113776-99-1) → 2-Adamantanone (700-58-3) + N-methylene-tert-butylamine (13987-61-6) + N-t-butylaziridinone (113777-00-7)

Conditions	Yield
With oxygen; methylene blue In chloroform-d1 at 15℃; for 1h; Irradiation;	A 100% B 16 % Chromat. C n/a

2-Adamantanone (700-58-3) + ethyllithium (811-49-4) → 2-ethyl-2-adamantanol (14648-57-8)

Conditions	Yield
In tetrahydrofuran at 0℃; for 2h; Inert atmosphere;	100%
Stage #1: 2-Adamantanone; ethyllithium In tetrahydrofuran; diethyl ether; benzene at 0 - 20℃; for 2h; Inert atmosphere; Stage #2: With ammonium chloride In tetrahydrofuran; diethyl ether; water; benzene Inert atmosphere;	94%
In tetrahydrofuran; benzene at 0℃;	94%
In diethyl ether; benzene

2-Adamantanone (700-58-3) + 1-azidohexane (6926-45-0) → 4-hexyl-4-azahomoadamantane (138956-35-1)

Conditions	Yield
With titanium tetrachloride In dichloromethane Ambient temperature;	100%
With titanium tetrachloride In dichloromethane at 20℃; for 16h; Schmidt insertion;	100%

2-Adamantanone (700-58-3) + sodium acetylide (1066-26-8) → 2-Ethynyl-2-hydroxyadamantane (70887-49-9)

Conditions	Yield
In tetrahydrofuran; xylene 1.) 18 h, room temp., 2.) 1 h, 70 deg C;	100%
In tetrahydrofuran; xylene a) RT, 18 h, b) 70 deg C, 1 h;	5.30 g

2-Adamantanone (700-58-3) + trimethylsulfoxonium iodide (1774-47-6) → 2-adamantanespiroxirane (24759-97-5)

Conditions	Yield
With potassium hydroxide In isopropyl alcohol for 1h; Reflux;	100%
With sodium hydroxide In isopropyl alcohol for 1h; Heating;	85%
With potassium tert-butylate In 1,2-dimethoxyethane for 18h; Heating;	85%
With sodium hydride Corey-Chaykovsky epoxidation;	65%
Epoxidation;

2-Adamantanone (700-58-3) + propyllithium (2417-93-8) → 2-Propyl-2-adamantanol (14451-85-5)

Conditions	Yield
In tetrahydrofuran at 0℃; for 2h; Inert atmosphere;	100%

2-Adamantanone (700-58-3) → 4-oxohomoadamantan-5-one (21898-84-0)

Conditions	Yield
With 3-chloro-benzenecarboperoxoic acid; scandium tris(trifluoromethanesulfonate) In dichloromethane for 0.333333h; Ambient temperature;	100%
With oxone; silica gel In dichloromethane at 20℃; for 1h; Baeyer-Villiger oxidation;	99%
With bis(2-phenyltrifluoromethanesulfonate)diselenide; dihydrogen peroxide In dichloromethane at 20℃; for 17h; Baeyer-Villiger oxidation;	99%

2-Adamantanone (700-58-3) → 1-adamantanol (700-57-2)

Conditions	Yield
With lithium vanadium(I) dihydride In tetrahydrofuran at 25℃; for 12h; Inert atmosphere;	100%
With manganese(III) (Z)-2,2,6,6-tetramethyl-5-oxohept-3-en-3-olate; phenylsilane; oxygen In 1,2-dichloro-ethane; isopropyl alcohol at 23℃; under 760 Torr;	99%
With ethanol; (ethylenebis(bicyclohexylphosphane))Ni(cis,cis-1,5-cyclooctadiene) In neat (no solvent) at 130℃; for 36h; Catalytic behavior;	99%

2-Adamantanone (700-58-3) → 2-adamantanone oxime (4500-12-3)

Conditions	Yield
With hydroxylamine hydrochloride; sodium acetate In ethanol at 60℃; for 2h;	100%
With hydroxylamine hydrochloride; sodium hydroxide In ethanol; water at 20℃;	95%
With hydroxylamine hydrochloride; sodium hydroxide In ethanol; water for 1h; Heating;	86%

2-Adamantanone (700-58-3) + acetonitrile (75-05-8) → 2-adamantaneylideneacetonitrile (38121-89-0)

Conditions	Yield
With potassium hydroxide In dimethyl sulfoxide for 10h; Reflux;	100%
With potassium hydroxide for 12h; Heating;	86%
With perhydrodibenzo-18-crown-6; potassium hydroxide Heating;	80%
With potassium hydroxide In dimethyl sulfoxide for 10h; Reflux;

2-Adamantanone (700-58-3) + nitromethane (75-52-5) + thiophenol (108-98-5) → 2-nitromethyl-2-phenylthioadamantane

Conditions	Yield
With piperidine In benzene for 36h; Heating;	100%

2-Adamantanone (700-58-3) + 3-(tetrahydropyran-2'-yloxy)propyne (6089-04-9) → 2-[3-(tetrahydro-pyran-2-yloxy)-prop-1-ynyl]-adamantan-2-ol

Conditions	Yield
Stage #1: 3-(tetrahydropyran-2'-yloxy)propyne With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 2h; Stage #2: 2-Adamantanone In tetrahydrofuran; hexane at -78℃; for 1h; Further stages.;	100%

2-Adamantanone (700-58-3) + 1,1-dilithio-2,3,4,5-tetraphenyl-1-silacyclopentadiene (157895-14-2) → 1-adamantan-2-ylidene-2,3,4,5-tetraphenyl-1H-silole

Conditions	Yield
In toluene at -78 - 20℃;	100%

2-Adamantanone (700-58-3) + diethylphosphonoacetic acid methyl ester → adamantylideneacetic acid methyl ester (98405-90-4)

Conditions	Yield
With sodium methylate In methanol; water	100%

2-Adamantanone (700-58-3) + 1,1'-biphenyl-2,2'-diamine (1454-80-4) → N,N'-di(2-adamantyl) 1,1'-biphenyl-2,2'-diamine (868127-50-8)

Conditions	Yield
Stage #1: 2-Adamantanone; 1,1'-biphenyl-2,2'-diamine With toluene-4-sulfonic acid In toluene for 72h; Heating / reflux; Stage #2: With lithium aluminium tetrahydride In tetrahydrofuran; toluene at 50℃; for 2h; Stage #3: With water; ammonium chloride In tetrahydrofuran; toluene	100%
With sodium tetrahydroborate; sulfuric acid In tetrahydrofuran; water at 20℃; for 5h;	74%

2-Adamantanone (700-58-3) → 2-n-butyladamantanol-2 (14451-86-6)

Conditions	Yield
Stage #1: 2-Adamantanone With n-butyllithium In diethyl ether at -78℃; for 0.166667h; Stage #2: With methanol	100%

2-Adamantanone (700-58-3) + hydrazinecarboxylic acid methyl ester (6294-89-9) → C12H18N2O2 (544419-63-8)

Conditions	Yield
With acetic acid In methanol for 1h; Reflux;	100%

2-Adamantanone (700-58-3) + toluene-4-sulfonic acid hydrazide (1576-35-8) → N'-(adamantan-2-ylidene)-4-methylbenzenesulfonohydrazide (41780-69-2)

Conditions	Yield
In methanol at 20℃; Schlenk technique;	100%
In methanol at 70℃; for 2h; Schlenk technique;

2-Adamantanone (700-58-3) + allyl bromide (106-95-6) → 1-adamantyl-3-buten-1-ol

Conditions	Yield
With ammonium acetate; zinc In tetrahydrofuran at 0℃; for 0.166667h; Inert atmosphere;	100%

Upstream product

• 814-78-8 3-Methyl-3-buten-2-one 
• 23695-65-0 adamantane-2-thione 
• 7314-85-4 2-adamantyl bromide 
• 281-23-2 adamantane 
• 1666-13-3 diphenyl diselenide 
• 201230-82-2 carbon monoxide 
• 124536-26-1 2-(2-Hydroperoxy-3-methyl-but-3-enyl)-isoindole-1,3-dione 
• 74087-85-7 3,3-dimethyldioxirane 
• 702-98-7 2-methyladamantan-2-ol 
• 1193-82-4 racemic methyl phenyl sulfoxide 
• 30541-56-1 adamantylidene-adamantane 
• 934-72-5 Methyl p-tolyl sulfoxide 
• 4500-12-3 2-adamantanone oxime 
• 68251-95-6 7-Adamantylidenbicyclo<4.1.0>heptan 

Downstream Products

• 66729-73-5 2,2-bis(phenylselenenyl)adamantane 
• 126255-67-2 2-(2-adamantylidene)propionic acid 
• 76481-47-5 2-(3'-chlorophenyl)-2-adamantanol 
• 875-72-9 2-methylideneadamantane 
• 29480-18-0 2-phenyladamantan-2-ol 
• 207285-51-6 tricyclo[3.3.1.1^3,7]decane-2-spiro-2'-(4',4'-diphenyl-1',3'-oxathiolan-5'-one) 
• 109610-24-4 2-(p-methoxy)benzyl-2-adamantanol 
• 19066-22-9 2-acetoxyadamantane 
• 700-57-2 1-adamantanol 
• 76300-20-4 adamantanone oxime O-benzyl ether 
• 113849-79-9 1-(2-Adamantylidene)-1-methoxy-1-phenylmethane 
• 298704-06-0 1-(2-Adamantylidene)-1-methoxy-1-(3-benzyloxyphenyl)methane 

Relevant articles and documents

Temperature deactivation of excited Tb3+ in the presence of 1,2-dioxetane in acetonitrile

Quenching the fluorescence (FL) of terbium perchlorate by 2,2'-adamantane-2,2'-dioxide (1) was shown to have a chemical character and was caused by the formation of the 3+> complex.The dependence of the lifetime (τ) of FL of Tb.3+ in acetonitrile on the temperature and concentration of 1 has been studied.The temperature dependence of τ is caused by rearrangement of the inner sphere of the aquasolvate complexes of Tb3+, which leads to the replacement of H2O with MeCN and 1.The energy of replacing the H2O molecule in the inner sphere of complexes with a solvent molecule has been calculated. - Key words: chemiluminiscence, fluorescence, Tb(ClO4)3*6H2O, 2,2'-adamantane-2,2'-dioxide, lifetime, quenching.

Solvent-cage effect (viscosity dependence) as a diagnostic probe for the mechanism of the intramolecular chemically initiated electron-exchange luminescence (CIEEL) triggered from a spiroadamantyl-substituted dioxetane

The excitation step of the intramolecular CIEEL generation in the triggered cleavage of spiroadamantyl-substituted dioxetane has been studied. The electron back-transfer (BET) process versus the direct chemiexcitation of the phenolate-anion emitter have been considered as mechanistic alternatives. The observed solvent-cage effect on the CIEEL generation, manifested by the increase of the singlet chemiexcitation yield at increased viscosity, provides evidence that the BET process operates in the intramolecular CIEEL mechanism.

NEW STABLE 1,2-DIOXETANE AND STERIC FACTORS IN THE OXIDATION OF SINGLET OXYGEN

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Highly selective production of 2-adamantanone by photocatalytic oxidation of adamantane

2-Adamantanone was selectively produced by photocatalytic oxidation of adamantane in acetic acid using TiO2 powders. The reactions were carried out at ambient and acetic acid reflux temperatures with and without an oxidant. Adding oxidant in refluxing acetic acid under irradiation remarkably increased conversion and selectivity. Rutile TiO2 powders showed better conversion and selectivity in the presence of H2O2. The total conversion was 67% and the highest selectivity of 2-adamanta-none was 89%. Copyright

STEREOISOMERIC DIOXETANES: THE EFFECT OF STRUCTURE ON THERMAL STABILITY AND EXCITATION YIELDS

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Selective and mild oxyfunctionalization of model polyolefins

The direct oxyfunctionalization of a model polyolefin, polyethylene-alt-propylene (PEP), was achieved utilizing a straightforward, mild process. In the presence of a manganese complex, manganese meso-tetra-2,6-dichlorophenylporphyrin acetate (Mn(TDCPP)OAc), imidazole, a phase transfer agent, and potassium peroxymonosulfate (Oxone), PEP was functionalized under ambient conditions without chain degradation. The primary oxidation products contained tertiary alcohols and ketones based on IR, 1H NMR, 13C NMR, and DEPT 13C NMR spectroscopy of the oxyfunctionalized products. The oxyfunctionalization of squalane, a small molecule, structural analogue of PEP, was also demonstrated. Spectroscopic analyses of the main products from the squalane oxidation were nearly identical with the functional groups identified in the PEP oxidation products. The degree of functionalization was modulated by changing the relative concentration of the oxidant, Oxone. The degree of functionalization and the thermal properties are reported for these new polymeric materials.

MECHANISM OF SENSITIZATION OF CHEMILUMINESCENCE IN THE THERMOLYSIS OF DIADAMANTYLIDENEDIOXETHANE

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Synthetic Methods and Reactions; 110. Fluorination of 1-Haloadamantanes and -diadamantane with Nitronium Tetrafluoroborate/Pyridine Polyhydrogen Fluoride or Sodium Nitrate/Pyridine Polyhydrogen Fluoride

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Zirconia-supported 11-molybdovanadophosphoric acid catalysts: effect of the preparation method on their catalytic activity and selectivity

The oxidation of adamantane with hydrogen peroxide catalyzed by zirconia-supported 11-molybdovanadophosphoric acid is shown to be a suitable green route for the synthesis of adamantanol and adamantanone. This work evaluates how the catalyst activity and selectivity are affected by some of its preparative parameters, such as the method for supporting the catalytically active heteropoly acid over the zirconia matrix or the pretreatments applied to the resulting materials before being used as heterogeneous catalysts. Our results indicate that the most effective catalysts able to maintain their activity after several reaction runs are those prepared by following the sol-gel route, whereas the most selective catalysts are those obtained by impregnation methods. Moreover, the calcination temperature has also been identified as a relevant parameter influencing the performance of catalysts based on supported heteropoly acids. The increasing catalytic activity observed over several consecutive reaction runs has been attributed to the formation of peroxo derivatives of polyoxometalate clusters at the surface of the catalyst and their accumulation after each reaction cycle.

Chemiluminescence and catalysis of the decomposition of dispiro(diadamantane-l,2-dioxetane) in solutions of lanthanide perchlorates 1: Catalysis of the 1,2-dioxetane decomposition

Decomposition of dispiro(diadamantane-l,2-dioxetane) u1, Cd1, Tb1, Pr1, and Ce1 perchlorates was studied by the chemiluminescencc method. The rate constants of decomposition of 1 in complexes of composition 1 Ln"1 and stability constants of these complexes, as well as activation parameters of the decomposition of 1 and thermodynamic parameters of the complexation were determined. A correlation between the thermodynamic parameters of complexation and ionic radii of Ln"1 was found.

Mechanism of RuO4-mediated oxidations of saturated hydrocarbons, isotope effects, solvent effects and substituent effects

Adamantane and 1,3,5,7-tetradeuterioadamantane were oxidized by RuO4 in two solvent systems, CCl4-CH3CN-H2O and acetone-water, yielding two kinetic deuterium isotope effects (KIEs), 4-8 ± 0-2 and 7.8 ± 0.l, respectively, very similar to those obtained in analogous reactions with cu-decalin and perdeuteriocis-decalin, 4-8 and 6-8. These results were interpreted as primary KIEs and small or negligible secondary KIEs. From this, sp2-hybridized intermediates were not involved in the reaction path. The kinetic effect of the solvent was investigated by performing the reaction in aqueous acetone and acetonitrile. The rates were correlated with Grunwald-Winstein Y values and with Reichardt ET(30) values. Both correlations showed the reaction to be only moderately dependent on the solvent polarity. 1-Substituted adamantanes were oxidized in CCl4-CH3CN giving a Taft ρ* value of -2.5 ± 0.1. These results were regarded as support for a reaction consisting of a pre-equilibrium with formation of a substrate-RuO4 complex followed by a rate-determining concerted reaction. Chemical Equation Presented. The results did not support a reaction mechanism with a carbocation or radical intermediate, or a scheme with two competing reactions, one with a carbocation intermediate and the other with a concerted mechanism.

QUANTUM-CHAIN PHOTOCATALYTIC DECOMPOSITION OF ADAMANTYLIDENEADAMANTANE-1,2-DIOXETANE INITIATED BY Eu*(fod)3

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Enhancing Chemo- And Stereoselectivity in C-H Bond Oxygenation with H2O2by Nonheme High-Spin Iron Catalysts- And Role of Lewis Acid and Multimetal Centers

Spin states of iron often direct the selectivity in oxidation catalysis by iron complexes using hydrogen peroxide (H2O2) on an oxidant. While low-spin iron(III) hydroperoxides display stereoselective C-H bond hydroxylation, the reactions are nonstereoselective with high-spin iron(II) catalysts. The catalytic studies with a series of high-spin iron(II) complexes of N4 ligands with H2O2 and Sc3+ reported here reveal that the Lewis acid promotes catalytic C-H bond hydroxylation with high chemo- and stereoselectivity. This reactivity pattern is observed with iron(II) complexes containing two cis-labile sites. The enhanced selectivity for C-H bond hydroxylation catalyzed by the high-spin iron(II) complexes in the presence of Sc3+ parallels that of the low-spin iron catalysts. Furthermore, the introduction of multimetal centers enhances the activity and selectivity of the iron catalyst. The study provides insights into the development of peroxide-dependent bioinspired catalysts for the selective oxygenation of C-H bonds without the restriction of using iron complexes of strong-field ligands.

Preparation method of adamantanone

The invention discloses a preparation method of adamantanone, and relates to the technical field of adamantanone synthesis. The problems that the reaction time is long and the operation process is tedious are solved. The preparation method specifically comprises the following steps: putting raw materials including adamantane, sulfuric acid and trifluoroacetic acid into a batching kettle, and stirring and mixing at 30 DEG C; raising the temperature to 50 DEG C, and introducing nitrogen into the batching kettle; pressing the mixed materials into a reaction tube, and performing standing for 1 minute; pouring the reaction solution on 500g of ice, adding a NaOH aqueous solution which is 7 times the weight of adamantane during cooling, and adjusting the pH value to 9; and extracting by using methylbenzene of which the weight is 3 times that of adamantane. The raw materials are mixed and then heated, nitrogen is introduced, then an oxidation reaction occurs, the retention time and temperatureof reaction liquid in a reaction tube are controlled in the leading-out period, the reaction liquid is extracted through methylbenzene and the NaOH aqueous solution, the extraction liquid is subjected to reduced pressure distillation concentration, cooling, separation and drying treatment, the final product is obtained, the operation process is relatively simple, the reaction is controllable, andthe time is short.